CN110294781B - Schiff base containing ferrocenyl thiadiazole base and preparation method thereof - Google Patents
Schiff base containing ferrocenyl thiadiazole base and preparation method thereof Download PDFInfo
- Publication number
- CN110294781B CN110294781B CN201910676424.2A CN201910676424A CN110294781B CN 110294781 B CN110294781 B CN 110294781B CN 201910676424 A CN201910676424 A CN 201910676424A CN 110294781 B CN110294781 B CN 110294781B
- Authority
- CN
- China
- Prior art keywords
- thiadiazole
- reaction
- amino
- schiff base
- eutectic solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Lubricants (AREA)
Abstract
Adding A mol of choline chloride and B mol of methanesulfonic acid into a dry three-neck flask, stirring at room temperature to obtain a eutectic solvent, then adding C mol of acetyl ferrocene and D mol of 2-amino-5-substituted-1, 3, 4-thiadiazole, carrying out reaction in a water bath at 40 ℃, and monitoring by TLC until the reaction is complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The method has the advantages of simple operation, high yield, high product purity, short reaction time, simple post-treatment, recyclable eutectic solvent, environmental protection and low cost, and has important significance for the synthesis and development of the compounds.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to ferrocenyl-containing thiadiazolyl Schiff base and a preparation method thereof.
Background
Schiff base has strong physiological activity and activity for preventing mould growth, and can be used as antibacterial, anticancer, antitumor, antituberculosis, etc.; and the complex formed by the Schiff alkali compound and the metal also has quite good oxygen-carrying activity; meanwhile, Schiff base and the complex thereof also have good catalytic activity and can be used as a catalyst in asymmetric synthesis and polymer synthesis. The method is characterized in that ferrocene and heterocyclic amine are simultaneously introduced into a compound to synthesize the Schiff base containing ferrocenyl thiadiazole base, and the method is bound to become a new hotspot of Schiff base research in the future.
The traditional Schiff base synthesis method uses Lewis acid as a catalyst and absolute ethyl alcohol as a solvent, has long reflux time, high reaction temperature and low yield and is not environment-friendly, so that the method for preparing the Schiff base containing the ferrocenyl thiadiazole base, which is simple to operate, high in yield, environment-friendly and low in cost, has certain significance.
Disclosure of Invention
The invention aims to provide a preparation method of Schiff base containing ferrocenyl thiadiazole base, which has the advantages of simple operation, high yield, high product purity, short reaction time, recyclable eutectic solvent, environmental protection and low cost.
In order to achieve the purpose, the invention adopts the technical scheme that:
the structural general formula of the Schiff base containing ferrocenyl thiadiazole is as follows:
wherein R is-H, -CH3，-C2H5，-C3H7-n，-SH，
，
，
，
，
，
，
，
，
，
，
，
，
，
。
The preparation method of the Schiff base containing ferrocenyl thiadiazole comprises the following steps:
adding A mol of choline chloride and B mol of methanesulfonic acid into a dry three-neck flask, stirring at room temperature to prepare a eutectic solvent, then adding C mol of acetyl ferrocene and D mol of 2-amino-5-substituted-1, 3, 4-thiadiazole, carrying out reaction in a water bath at 40 ℃, and monitoring by TLC until the reaction is complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base.
The general structural formula of the acetyl ferrocene is shown as follows:
the structural general formula of the 2-amino 5-substituted-1, 3, 4-thiadiazole is as follows:
wherein R is-H, -CH3，-C2H5，-C3H7-n，-SH，
，
，
，
，
，
，
，
，
，
，
，
，
，
。
And (3) monitoring by TLC, wherein the developing solvent used is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 5: 1.
Compared with the prior art, the invention has the beneficial effects that:
according to the preparation method of the Schiff base containing ferrocenyl thiadiazole, acetyl ferrocene and 2-amino-5-substituted-1, 3, 4-thiadiazole are used as raw materials, a eutectic solvent choline chloride-methanesulfonic acid is used as a solvent and a catalyst, and the Schiff base containing ferrocenyl thiadiazole can be prepared at a high yield. The method has the advantages of simple operation, high yield, high product purity, short reaction time, recyclable eutectic solvent, environmental protection, low cost and great application prospect.
Drawings
FIG. 1 is an IR spectrum of acetyl ferrocene condensed 2-amino-1, 3, 4-thiadiazole Schiff base prepared in example 1
FIG. 2 is the IR spectrum of 2-amino-5-methyl-1, 3, 4-thiadiazole Schiff base as prepared in example 2
FIG. 3 is the IR spectrum of 2-amino-5-ethyl-1, 3, 4-thiadiazole Schiff base as prepared in example 3
FIG. 4 is the IR spectrum of 2-amino-5-n-propyl-1, 3, 4-thiadiazole Schiff base as prepared in example 4
FIG. 5 is the IR spectrum of 2-amino-5-mercapto-1, 3, 4-thiadiazole Schiff base as prepared in example 5
FIG. 6 is an IR spectrum of 2-amino-5- (4-pyridyl) -1,3, 4-thiadiazole Schiff base as prepared in example 6
FIG. 7 is an IR spectrum of 2-amino-5-phenyl-1, 3, 4-thiadiazole Schiff base as prepared in example 7
FIG. 8 is a drawing of the preparation of acetylferrocene 2-amino-1, 3, 4-thiadiazole Schiff base from example 11H NMR spectrum
FIG. 9 is a drawing of the preparation of acetylferrocene 2-amino-5-methyl-1, 3, 4-thiadiazole Schiff base from example 21H NMR spectrum
FIG. 10 shows the preparation of acetylferrocene condensed 2-amino-5-ethyl-1, 3, 4-thiadiazole Schiff base in example 31H NMR spectrum
FIG. 11 is a drawing of the preparation of acetylferrocene 2-amino-5-n-propyl-1, 3, 4-thiadiazole Schiff base from example 41H NMR spectrum
FIG. 12 is a drawing of the preparation of acetylferrocene 2-amino-5-mercapto-1, 3, 4-thiadiazole Schiff base from example 51H NMR spectrum
FIG. 13 is a photograph of 2-amino-5- (4-pyridyl) -1,3, 4-thiadiazole Schiff base as prepared in example 61H NMR spectrum
FIG. 14 is a drawing of the preparation of acetylferrocene 2-amino-5-phenyl-1, 3, 4-thiadiazole Schiff base from example 71H NMR spectrum.
Detailed Description
The following is a further detailed description of the invention with reference to examples:
the invention takes acetyl ferrocene and 2-amino-5-substituted-1, 3, 4-thiadiazole as raw materials, and takes choline chloride-methanesulfonic acid as a eutectic solvent as a solvent and a catalyst to prepare a series of Schiff bases containing ferrocenyl thiadiazole. The reaction equation is as follows:
wherein R is H, CH3，C2H5，C3H7N (n-propyl), SH,
,
example 1 preparation of acetylferrocene 2-amino-1, 3, 4-thiadiazole Schiff base:
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.12g (1.2mmol) 2-amino-1, 3, 4-thiadiazole were added and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 94.2%, and the melting point is 148-149 ℃.
IR(KBr) ν: 3301cm-1,3089cm-1(ν Ferrocene C-H); 2923cm-1 (ν CH3); 1375cm-1(ν CH3) ; 1604cm-1(ν C=N);1504cm-1,1423cm-1 (ν Thiadiazole ring);1113cm-1 (ν C-S-C); 825cm-1 (ν Ferrocene C-H) ;490cm-1 (ν N-C-S) ;
1H NMR(400 MHz, DMSO-d6) δ: 2.03(3H,-CH3Singlet), 4.23(5H, Fc-H, triplet), 4.47(2H, Fc-H, multiplet), 4.79(2H, Fc-H, multiplet), 8.60 (1H, -H, singlet).
Example 2 preparation of Acetylferrocene 2-amino-5-methyl-1, 3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.14g (1.2mmol) 2-amino-5-methyl-1, 3, 4-thiadiazole were added and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 90.3%, and the melting point is 150-152 ℃.
IR(KBr) ν: 3426cm-1 (ν FerroceneC-H); 2925cm-1 (ν CH3); 1377cm-1 (ν CH3) ; 1605cm-1(ν C=N); 1527cm-1,1427cm-1 (ν Thiadiazole ring); 1104cm-1 (ν C-S-C); 828cm-1,(ν FerroceneC-H); 648 cm-1,495cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ: 2.05(3H,-CH3Singlet), 2.51(3H, -CH)3Singlet), 4.26(5H, Fc-H, triplet), 4.53(2H, Fc-H, multiplet), 4.80(2H, Fc-H, multiplet).
Example 3 preparation of Acetylferrocene 2-amino-5-ethyl-1, 3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.15g (1.2mmol) 2-amino-5-ethyl-1, 3, 4-thiadiazole were added and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 91.7%, and the melting point is 145-146 ℃.
IR(KBr) ν: 3291cm-1,3114cm-1 (ν FerroceneC-H); 2928cm-1 (ν CH3); 1742cm-1, 1380cm-1(ν CH3); 1618cm-1 (ν C=N,s); 1526cm-1,1458cm-1 (ν Thiadiazole ring); 1112cm-1 (ν C-S-C); 787cm-1(ν FerroceneC-H); 694 cm-1,478cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ: 1.24(3H,-CH3Triplet), 2.09(3H, -CH)3Singlet), 2.79(2H, -CH)2-, multiplet), 4.26(5H, Fc-H, triplet), 4.49(2H, Fc-H, multiplet), 4.85(2H, Fc-H, multiplet).
Example 4 preparation of Acetylferrocene 2-amino-5-n-propyl-1, 3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid are added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.17g (1.2mmol) 2-amino-5-n-propyl-1, 3, 4-thiadiazole are added and the reaction is carried out in a water bath at 40 ℃ and monitored by TLC until the reaction is complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 97.2%, and the melting point is 164-168 ℃.
IR(KBr) ν: 3423cm-1,3160cm-1 (ν FerroceneC-H);2926cm-1 (ν CH3);1612cm-1 (ν C=N) ; 1526cm-1,1459cm-1 (ν Thiadiazole ring); 1097cm-1,1010 cm-1 (ν C-S-C);813cm-1 (ν FerroceneC-H) ;661 cm-1,472cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:0.96(3H,-CH3Triplet), 1.63(2H, -CH)2-, multiplet), 2.06(3H, -CH3Singlet), 2.93(2H, -CH)2-, triplet), 4.32(5H, Fc-H, triplet), 4.66(2H, Fc-H, multiplet), 4.97(2H, Fc-H, multiplet).
Example 5 preparation of Acetylferrocene 2-amino-5-mercapto-1, 3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask, and the mixture was stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.16(1.2mmol) 2-amino-5-mercapto-1, 3, 4-thiadiazole were added, and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 94.1 percent, and the melting point is 161-164 ℃.
IR(KBr) ν: 3294cm-1,3177cm-1 (ν FerroceneC-H);2925cm-1 (ν CH3);1375cm-1 (ν CH3);1617cm-1 (ν C=N);1559cm-1,1507cm-1 (ν Thiadiazole ring); 1105cm-1(ν C-S-C); 825cm-1 (ν FerroceneC-H); 621 cm-1,484cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:2.10(3H,-CH3Singlet), 4.20(5H, Fc-H, triplet), 4.64(2H, Fc-H, multiplet), 4.91(2H, Fc-H, multiplet), 7.22(1H, N-H, singlet).
EXAMPLE 6 preparation of Acetylferrocenyl 2-amino-5- (4-pyridyl) -1,3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.21g (1.2mmol) 2-amino-5- (4-pyridyl) -1,3, 4-thiadiazole were added and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 96.9 percent, and the melting point is 196-199 ℃.
IR(KBr) ν: 3295cm-1(ν FerroceneC-H);3089cm-1,745 cm-1 (ν Pyridine ring ) ;2775cm-1(ν C thiadiazole-C pyridine); 2866cm-1(ν CH3) ; 1283cm-1 (ν CH3);1611cm-1 (ν C=N,s);1523cm-1,1498cm-1,(ν C=N); 1106cm-1(ν C-S-C); 804cm-1 (ν FerroceneC-H) ; 603 cm-1,431cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) Delta.2.07 (3H, -CH3, singlet), 4.12(5H, Fc-H, triplet), 4.52(2H, Fc-H, multiplet), 4.78 (2H, Fc-H, multiplet), 7.92, 8.22, (4H, pyridy-H, multiplet).
Example 7 preparation of Acetylferrocenyl 2-amino-5-phenyl-1, 3, 4-thiadiazole Schiff base
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask and stirred at room temperature to obtain a eutectic solvent, then 0.23g (1mmol) acetylferrocene and 0.21g (1.2mmol) 2-amino-5-phenyl-1, 3, 4-thiadiazole were added and the reaction was carried out in a water bath at 40 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain a crude product, and the eutectic solvent can be obtained again after the water phase is recovered. Recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base. The yield is 96.8%, and the melting point is 182-184 ℃.
IR(KBr) ν: 3292cm-1 (ν FerroceneC-H);3089cm-1 (ν N-H); 3036cm-1 (ν Phenyl ring C-H ); 2917cm-1(ν C thiadiazole-C benzene) ; 1461cm-1 (ν CH3); 1617cm-1, (ν C=N)1547cm-1,1501cm-1,(ν C=N); 1112cm-1(ν C-S-C); 806cm-1 (ν FerroceneC-H); 643 cm-1,486cm-1 (ν N-C-S)。
1H NMR(400 MHz, DMSO-d6) δ:2.05(3H,-CH3Singlet), 4.17(5H, Fc-H, triplet), 4.37(2H, Fc-H, multiplet), 4.62 (2H, Fc-H, multiplet), 7.72,7.96,8.06, (5H, Ph-H, multiplet).
Example 8 the aqueous phase was distilled to recover the eutectic solvent. The influence of the cyclic use of the eutectic solvent on the final yield is explored by taking acetyl ferrocene-2-amino-5-phenyl-1, 3, 4-thiadiazole Schiff base as an example, and the result is shown in Table 1.
TABLE 1 Effect of eutectic solvent recycle on yield
| Number of cycles | Yield (%) |
| 1 | 96.8 |
| 2 | 96.2 |
| 3 | 95.5 |
| 4 | 94.7 |
| 5 | 93.3 |
The result shows that the yield is not greatly influenced by recycling the eutectic solvent for five times, and the eutectic solvent still has a good catalytic effect on the reaction, which indicates that the method is simple, efficient and environment-friendly.
Claims (3)
1. A preparation method of Schiff base containing ferrocenyl thiadiazole is characterized by comprising the following steps:
reacting acetyl ferrocene and 2-amino-5-substituted-1, 3, 4-thiadiazole in a choline chloride-methanesulfonic acid eutectic solvent to obtain ferrocenyl thiadiazole Schiff base;
the 2-amino 5-substituted-1, 3, 4-thiadiazole has the structural general formula as follows:
wherein R is-H, -CH3，-C2H5，-n-C3H7，-SH，
The choline chloride-methanesulfonic acid eutectic solvent is obtained by fully mixing choline chloride and methanesulfonic acid according to the molar ratio of 1 (1-2);
the molar ratio of the acetyl ferrocene to the 2-amino-5-substituted-1, 3, 4-thiadiazole is 1 (1.1-1.2).
2. The method according to claim 1, characterized by the following specific steps:
adding choline chloride and methanesulfonic acid into a dry three-neck flask, stirring at room temperature to prepare a eutectic solvent, then adding acetyl ferrocene and 2-amino-5-substituted-1, 3, 4-thiadiazole, reacting in a water bath at 40 ℃, and monitoring by TLC until the reaction is complete; after the reaction is finished, pouring the reaction solution into water, extracting with dichloromethane, evaporating to remove the solvent to obtain a crude product, and recovering the water phase to obtain a eutectic solvent again; recrystallizing the crude product by absolute ethyl alcohol to obtain a pure product containing ferrocenyl thiadiazole Schiff base.
3. The method of claim 2, wherein the TLC is used for monitoring the reaction, the reaction is completed when the raw material point disappears, and the developing agent of the TLC is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 5: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910676424.2A CN110294781B (en) | 2019-07-25 | 2019-07-25 | Schiff base containing ferrocenyl thiadiazole base and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910676424.2A CN110294781B (en) | 2019-07-25 | 2019-07-25 | Schiff base containing ferrocenyl thiadiazole base and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110294781A CN110294781A (en) | 2019-10-01 |
| CN110294781B true CN110294781B (en) | 2022-04-12 |
Family
ID=68031856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910676424.2A Active CN110294781B (en) | 2019-07-25 | 2019-07-25 | Schiff base containing ferrocenyl thiadiazole base and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110294781B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627783B (en) * | 2019-10-23 | 2021-11-16 | 陕西科技大学 | Preparation method of Schiff base containing carbazolyl and oxadiazolyl or thiadiazolyl |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104558057A (en) * | 2015-01-19 | 2015-04-29 | 陕西科技大学 | Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole |
| CN109970817A (en) * | 2019-03-26 | 2019-07-05 | 陕西科技大学 | A method of preparing acyl Ferrocene diazanyl dithioester Schiff |
-
2019
- 2019-07-25 CN CN201910676424.2A patent/CN110294781B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104558057A (en) * | 2015-01-19 | 2015-04-29 | 陕西科技大学 | Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole |
| CN109970817A (en) * | 2019-03-26 | 2019-07-05 | 陕西科技大学 | A method of preparing acyl Ferrocene diazanyl dithioester Schiff |
Non-Patent Citations (4)
| Title |
|---|
| Dawei Yin等.Ferrocene-Based with Thiadiazole Antibacterial Agents: Synthesis, Characterization, and Biological Evaluation.《Applied Mechanics and Materials》.2012,第189卷第181-184页. * |
| Ferrocene-Based with Thiadiazole Antibacterial Agents: Synthesis, Characterization, and Biological Evaluation;Dawei Yin等;《Applied Mechanics and Materials》;20120726;第189卷;第181-184页 * |
| 刘玉婷等.无溶剂研磨法合成酰基二茂铁2-氨基-5-取代-1,3,4-噻二唑Schiff碱.《精细石油化工》.2018,第35卷(第1期),第1-5页. * |
| 无溶剂研磨法合成酰基二茂铁2-氨基-5-取代-1,3,4-噻二唑Schiff碱;刘玉婷等;《精细石油化工》;20180131;第35卷(第1期);第1-5页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110294781A (en) | 2019-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5171640B2 (en) | 2,2 ', 6,6'-tetraoxazoline biphenyl ligand and method for preparing the same | |
| CN103649055A (en) | Method for manufacturing pyrazole derivative | |
| CN110294781B (en) | Schiff base containing ferrocenyl thiadiazole base and preparation method thereof | |
| CN108794412B (en) | Preparation method of 4, 5-diaryl-2H-1, 2, 3-triazole compound | |
| CN100497309C (en) | Method for synthesizing heteroaryl thiosemicarbazone antineoplastic | |
| CN115286594B (en) | With S 8 Method for synthesizing quinone thiazole compounds as raw materials | |
| CN109553611A (en) | The preparation method and purposes of Rivaroxaban intermediate | |
| CN105348202B (en) | A kind of method that different luminol is prepared using phthalylhydrazine as raw material | |
| CN110128413B (en) | 5-acetyl-4- (N-substituted carbazolyl) -6-methyl-3, 4-dihydropyrimidine-2-ketone and preparation method thereof | |
| CN111100085A (en) | Preparation method of 3-aryl-2H-benzo [ β ] [1,4] benzoxazine-2-one compound | |
| CN111484455A (en) | Synthetic method of 2-chloro-5-fluoro-6-methylpyrimidine | |
| CN106432217A (en) | Schiff base containing carbazolyl group and oxadiazole group and preparing method thereof | |
| CN105148998A (en) | Catalyst composition and application thereof | |
| CN103694189A (en) | Synthesis method of 2-oxazole or 2-thiazole | |
| CN111662235B (en) | Benzoyl pyridazine derivative and preparation method thereof | |
| US3130218A (en) | Process for the preparation of 4-nitrostilbene carbonitriles | |
| CN113856764B (en) | Transition metal catalyst and preparation method and application thereof | |
| CN109796348B (en) | 9-benzyl naphthylamine and synthesis method thereof | |
| CN110590760B (en) | 2, 1-benzisoxazole derivative and synthetic method and application thereof | |
| Horvath et al. | Synthesis of new 2-phenylamino-5-[(α-acylamino)-pX-stiryl]-1, 3, 4-thiadiazole compounds | |
| US3268529A (en) | 3-cyanoalkyl substituted 4-(3h)-quinazolinones | |
| CN113956209B (en) | Preparation method of NH-1,2, 3-triazole compound | |
| CN110627783B (en) | Preparation method of Schiff base containing carbazolyl and oxadiazolyl or thiadiazolyl | |
| CN110577520B (en) | Preparation method of 6-nitro-4-substituted amino quinazoline derivative | |
| JP5208928B2 (en) | C2-ruthenocene bisphosphine ligand having only symmetric planar chirality and its synthesis method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |